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2019 Predictions | When Will Southwest Hawaii Flights Start, Pricing & More!

Exciting times. As 2018 draws to a rapid conclusion, it’s time to review 2019 predictions.

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297 thoughts on “2019 Predictions | When Will Southwest Hawaii Flights Start, Pricing & More!”

  1. When will American make improvements on plans from Phoenix to Maui? It’s our only non stop options and the planes seem much older.

  2. There will be 6 of us traveling to Maui from Denver 12/14-12/21 per timeshare dates. Has been around 1100 round trip. When do u suggest buying & what is a good price for that time of year? thank you

    1. Hi Jennifer.

      Not sure your dates will improve. If you come a day earlier (return as planned) you can go on the nonstop for $705.

      Aloha.

  3. Do you thing Southwest or Hawaiian Airlines will offer Inter-island Coupon books like 35 years

    ago between Hawaiian and Aloha Airlines???

  4. My husband and I are looking to travel to Maui to celebrate our 10 year wedding anniversary with our two young kids kids this coming July for 10 days. We would like to be there on our anniversary date – July 12th so other than that dates are flexible before and after. Should we book now or wait it out a little longer for a possible price drop. Traveling from SAN to OGG. Thanks!

  5. Going from Los Angeles to Lihue in Jan. 20, 2019. Any idea when might be best time to buy tickets? Thanks for your input.

  6. Looking for 2 tickets PDX to OGG Oct. 6 to Oct. 13, 2018. I see direct is about $640, which seems a bit high for October. Thinking of waiting as about 6 months out and October is usually a low season month, would you agree?

  7. Aloha!

    Family of 6 looking to travel from OAK to HNL 10/4/18-10/11/18. Hawaiian Airlines is $471 as of right now. Since we’re 6 months out and traveling during low season, do you think prices will drop? Should we wait closer to our travel dates to purchase? We would love your advice, please. Thank you in advance!

    Mahalo,

    Liu

    1. Hi Liu.

      Yes do wait on that route for your dates. Target price is about $100 less than currently available. Can’t say when it will happen, but we are always reporting on those fares, so stay tuned and we’ll have those coming up later in spring or during summer. Don’t rush to buy.

      Aloha.

  8. Hello! I have a timeshare in Maui and have to work with the dates 8/12 – 8/19. I’m seeing flights now for between $530 and $600. We are still 4.5 months out from travel, do you think I should wait to purchase to see if the race to Hawaii continues to lower prices or have we capped out on that benefit?

    I am traveling from LAX to OGG on 8/12/-8/19 (timeshare restrictions). There are fares available currently from about $530 to $600. Do you think prices will get lower, or should I book now? Thanks for your thoughts!Thanks for your thoughts!

    1. Hi Erina.

      Looks like low $500’s which isn’t bad to lock in. Could come down by say $50, but you would probably need to change to mid-week dates, which appears to not be possible. Your weekend flights will remain more expensive. We’d suggest buying.

      Aloha.

  9. Aloha,

    I’m looking for flights from PDX to Honolulu June 9th, then an inter island Hopper a few days later, and returned from OGG to PDX on June 21st.

    I’ve been watching airfare for the past couple of months and have seen it go from $800 down to $500, and then saw $100 per person hike last night so my total for two people was around $1600 with taxes and fees.

    This morning I’m now finding Hawaiian has this itinerary at $500 again.

    Some web sites say to buy now. Other websites say to wait until around 6 weeks before my trip, as it will be a significant price drop.

    What says the Best of Hawaii?

    😎 So excited for this trip… I haven’t been to the islands in 15 years, and I’m bringing my oldest child for the first time as her high school graduation present!!

    Mahalo, Becky

    PS – just to see if I could, I went to book the $500 round-trip flight this morning, and when I went to hit submit it timed out and refreshed with a $740 per person price…

    So I’m guessing what I saw was a glitch in the system, or a window I had open from last night.

    1. Hi Becky.

      $584 on Hawaiian as of right now. Not a bad price. Complication is two-fold: 1) flying on Saturday and 2) return is in very high priced season. Suggest buying now as it is doubtful that it will go down due to complication indicated.

      Also on your PS, try clearing your browser cache or using a different browser and see if you get any different results.

      Aloha.

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